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craigslist

Vacation Rentals in Chicago

  1. see also
  2. Stunning 1BR condo in SoNo West!
    $1,800
    Chicago
  3. Penn State Football Package
    $999
    Evanston
  4. Gold Coast Lake Michigan Corner Stidio
    $1,800
    Chicago
  5. Wisconsin Dells - Glacier Canyon Nov 20-22 w/8 waterpark wristbands
    $299
    Wisconsin Dells
  6. Modern and Well-Equipped Cabin in Minocqua, WI.
    $0
    Gurnee
  7. Wyndham Glacier Canyon at The Wilderness 10/24-26
    $695
    north chicagoland
  8. 2 Bedroom Aframe
    $0
    city of chicago
  9. Marriott's Aruba Ocean Club (July 20, 2026 to July 27, 2026)
    $2,700
    Palm Beach Aruba
  10. 5 STAR RESORT - GREAT Amenities + Full Kitchen
    $900
    WORLDWIDE
  11. Wisconsin Dells-Glacier Canyon Nov 6-8 2 bdrm Pres w/ 6 wristbands
    $299
    Wisconsin Dells
  12. Cabin for rent
    $200
    seveirville
  13. 4 Bdrm Private Pool/Spa Home
    $4,000
    Palm Desert
  14. Wisconsin dells Glacier canyon
    $0
    Fredonia
  15. Fall Colors Waterfront Cottages
    $135
    Barryton
  16. New Years Eve and Independence Day week
    $800
    Wisconsin Dells, Wi.
  17. Wisconsin Dells - Glacier Canyon Oct 31-Nov 2 w/ 4 wrtpk wristbands
    $249
    Wisconsin Dells
  18. Wisconsin Dells-Glacier Canyon Oct 29-Nov 1 2 Pres w/ 6 wrstbnds
    $199
    Wisconsin Dells
  19. Wisconsin Dells-Glacier Canyon Oct 27-30 3 bdrm Pres w/8 wristbands
    $249
    Wisconsin Dells
  20. Smokey Mountain Fall vacatiion
    $850
    Gaitlinburg
  21. Attention snowmobilers
    $3,500
    Presque Isle
  22. rci points for sale
    $200
    fredonia
  23. Modern Recent home
    $125
    Chicago
  24. Vacation home available for rent
    $3,695
    Chicago
  25. Assistance for right girl or couple
    $0
    city of chicago
  26. Perfect for groups
    $0
    Chicago, IL
  27. Ideally located in West Lakeview withing walking distance to Wrigley Field
    $135
    Chicago, IL
  28. Perfect for groups
    $0
    Chicago, IL
  29. Visiting the Evanston area for 3 days or more? Check us out.
    $269
    Evanston IL
  30. $$$ Part time work to cover Rent for Ladies18-35 Apply now $$$$$
    $0
    city of chicago
  31. Old Naples Florida resort rental. Near Beach. Jan 10th thru Jan 17th
    $1,975
    Naples
  32. 2 Bedroom 16x80 Manufactured Home
    $2,150
    St. Cloud, Fl.
  33. Perfect for groups
    $135
    Chicago, IL
  34. Perfect for groups
    $135
    Chicago, IL
  35. Perfect for groups
    $135
    Chicago, IL
  36. Perfect for groups
    $135
    Chicago, IL
  37. Furnished motel style suite, No Deposit daily $ 75.00 weekly $395
    $395
    Bartlett ILLINOIS 60103
  38. Furnished motel style suite, No Deposit daily $ 75.00 weekly $ 375
    $395
    Bartlett ILLINOIS 60103
  39. Wisconsin Dells - Glacier Canyon Oct 27-30 w/8 waterpark wristbands
    $199
    Wisconsin Dells
  40. Wisconsin Dells - Glacier Canyon Oct 21-23 w/8 waterpark wristbands
    $199
    Wisconsin Dells
  41. Scottsdale Arizona Luxury Condominium Pool Side Clubhouse view
    $5,500
    scottsdale
  42. Hotel rooms available discounted rates
    $0
    city of chicago
  43. 3br -Tropical Caribbean Vacation this Winter St John US Virgin Islands
    $5,899
    St John USVI
  44. $1,800 / 1br - New Years Ski Adventure (12/26/25-1/2/26)
    $1,800
    Vail, CO
  45. Lovely unit
    $1,600
    Chicago
  46. Furnished motel style suite, No Deposit daily $ 75.00 weekly $ 350
    $395
    Bartlett ILLINOIS 60103
  47. Furnished motel style suite, No Deposit $ 70 daily $ 395 weekly
    $395
    Bartlett ILLINOIS 60103
  48. WINTER VACATION HOME
    $3,000
    Minocqua
  49. WELL-MAINTAINED CONDO
    $1,300
    Schaumburg
  50. Perfect for groups
    $150
    Chicago, IL
  51. ~*~ Luxury FL Beach Rental 6br/5ba/over 3k sqft/sleeps 16 ~*~
    $0
    Cape San Blas, FL
  52. 3br 2bath beach condo
    $0
    Panama City beach florida
  53. Condo - Bradenton Florida - Seasonal Rental
    $1,600
    Bradenton
  54. A Home Away From Home
    $150
    Chicago
  55. Perfect for groups
    $150
    Chicago, IL
  56. New construction elevator building
    $150
    Chicago, IL
  57. Amazing Southern City Views Spacious 1 Bed 1 Bath
    $1,350
    Chicago
  58. ROOM 4 RIOT FEST
    $200
    Douglass Park
  59. A Vacation Rental Home Away from Home
    $150
    Chicago, IL
  60. Just steps from vibrant downtown Naperville
    $1,300
    Naperville
  61. Home for rent
    $3,750
    Beverly
  62. 3 bedroom, 2 bath residence offers private outdoor space
    $4,408
    Chicago